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This area was occupied by indigenous peoples for thousands of years. At the time of English encounter, it was territory of the Paugusset (an Algonquian-speaking tribe). English colonists affiliated with the contemporary New Haven Colony purchased land which today comprises Milford, Orange, and West Haven on February 1, 1639 from Ansantawae, chief of the local Paugusset. They knew the area as Wepawaug, named for the small river which runs through the town. Later the settlers named streets in both Milford and Orange as Wepawaug.
The settlers built a grist mill by the Wepawaug River in 1640, to take advantage of its water power.

During the Revolutionary War, the Milford section of the Boston Post Road, a vital route connecting Boston, New York and other major coastal cities, was blockaded by Continental forces, and Fort Trumbull was constructed to protect the town. The site of the blockade is commemorated by the Liberty Rock monument.

By 1822, the town had grown large enough that residents in the northern and eastern sections of Milford chartered the Town of Orange. During the next century and a half, the remaining section of Milford was known for shipbuilding, farming and oystering. Some industrial facilities were also developed in town.

Because of its location on Long Island Sound, during the later 19th century, Milford also became known as a beach resort for residents of New Haven and Bridgeport.

In 1899, the “Memorial Bridge” (a “stone bridge and tower commemorating the town’s history and founders”) replaced the last mill over the Wepawaug, which had closed in 1894. The bridge was described as “simple in design, its broad copings surmounted with rough hewn blocks of granite, bearing the names of the first settlers. There are ten blocks on the south and twenty o

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